反応 #2286393
ord-e4f4b799d6af4d91adebaae81f2027f1
反応方程式
溶媒
反応条件
後処理
- 1その他The flask was fitted with a reflux condenser
- 2温度was heated to reflux
- 3温度the reaction was cooled in an ice bath
- 4その他partitioned between aqueous saturated NaHCO3 and ethyl acetate
- 5その他The layers were separated
- 6抽出the aqueous layer was extracted once with ethyl acetate
- 7洗浄The combined organics were washed once with brine
- 8乾燥dried over MgSO4
- 9ろ過filtered
- 10濃縮concentrated
- 11その他This solid was triturated with 20% ethyl acetate/hexanes
- 12ろ過The solids were filtered off
- 13その他the filtrate evaporated
- 14その他to provide a residue which
- 15その他was purified via silica gel column chromatography (0 to 100% ethyl acetate/hexanes)
実験手順
To a 3-neck round bottom flask was added fluoropyridine boronic acid (4.55 g, 32.3 mmol), ethanol (54 mL), and aqueous K2CO3 solution (27 mL, 2.0 M, 53.8 mmol), followed by 50 mL toluene. To this mixture was added di(tert-butyl) 2-bromo-1,3-thiazol-5-ylimidodicarbonate (10.2 g, 26.9 mmol). Next, tetrakis(triphenylphosphine)palladium(0) (6.2 g, 5.4 mmol) was added in one portion. The flask was fitted with a reflux condenser and was heated to reflux. After 45 minutes, the reaction was cooled in an ice bath and partitioned between aqueous saturated NaHCO3 and ethyl acetate. The layers were separated and the aqueous layer was extracted once with ethyl acetate. The combined organics were washed once with brine, dried over MgSO4, filtered, and then concentrated. This solid was triturated with 20% ethyl acetate/hexanes. The solids were filtered off and the filtrate evaporated to provide a residue which was purified via silica gel column chromatography (0 to 100% ethyl acetate/hexanes) to afford the desired product as an off-white solid (7.74 g, 73% yield): mp 94-96° C.; 1H NMR (300 MHz, CDCl3) δ 8.91 (app t, J=1.3 Hz, 1H), 8.52 (d, J=3.0 Hz, 1H), 7.96 (ddd, J=9.2, 3.0, 1.8 Hz, 1H), 7.66 (s, 1H), 1.48 (s, 18H); ESIMS m/z 396 (M+1).